


The Prettiest Princess

by Fallynleaf



Category: Supernatural
Genre: Dean Doing Feminine Things, Gen, John Winchester's A+ Parenting, Pre-Series, Pretty Pretty Princess
Language: English
Status: Completed
Published: 2014-10-14
Updated: 2014-10-14
Packaged: 2018-02-21 03:43:58
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,662
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2453456
Author URL: https://archiveofourown.org/users/Fallynleaf/pseuds/Fallynleaf
Summary: <blockquote class="userstuff">
              <p>Among the stolen girl's presents that Dean attempted to give Sam on Christmas in 1991, there was a board game. A very special, very <i>girly</i> board game. It was everything that John would not want his sons to associate with. Which, of course, was the entire point of playing it.</p>
<p>The tagline for this fic is, to misquote an article I once read, <i>"sometimes children play with toys in subversive ways"</i></p>
            </blockquote>





	The Prettiest Princess

**Author's Note:**

> Pretty Pretty Princess is a board game that is very near and dear to my heart. I first played it when I was already long past the target age demographic, but it somehow became a significant part of my adolescence anyways.
> 
> My first concept of Sam and Dean playing Pretty Pretty Princess was entirely a joke. But then I did a little research, and I discovered that the events of the canon universe and our real life universe managed to line up just so, and it turns out that Pretty Pretty Princess was invented in 1990, which happens to be one year before the flashback sequences in "A Very Supernatural Christmas" took place.
> 
> And after that, it was easy to slip Pretty Pretty Princess under the tree with the rest of the girly presents.
> 
> A bit of a warning: if you are expecting a happy, light crack!fic, this is not it.
> 
> Also, there now exists a sequel of sorts to this fic! See the end note for more information.

There was another package, bigger than the rest, that rustled nicely when you shook the box. Dean had saved this present, because the bigger ones were always more exciting to open, and he had hopes that it might contain Legos, and he wanted to surprise Sam with it a little bit later to draw out Christmas morning as long as possible.

But after the reveal, the stolen presents lost their appeal because they weren't even toys that Sam and him could use. So Dean forgot about the last wrapped package entirely.

That is, until Sam tripped over it where it lay partially exposed under the tree and put a sizeable tear in the garish wrapping paper. Turquoise and pink showed through the tear, heralding nothing good.

"What's this?" Sam asked, picking up the box. He held it up to his ear and shook it.

"Dunno," Dean said. "Probably something for girls, though."

Sam shrugged and hooked his fingers into the wrapping paper. He tore it off in long strips, gradually revealing an image of three children seated around a white table with a pastoral backdrop, each of them wearing grins that were honestly a little creepy. Twin castles embellished the bucolic setting.

"Pretty Pretty Princess," Sam read. "The jewelry dress-up game."

It was the girliest thing Dean had ever seen. It was the embodiment of everything frivolous and superficial and inane, and for one fleeting moment, Dean wished he could have it. Wished that him and Sam could've grown up just thinking that fantasy was all unicorns and princesses in castles, and not real-life werewolves that tore out your heart in a dead cityscape.

Sam set down the box with a sigh. It rattled with false promise. "Kind of hoped it would be Legos," Sam admitted. "Girls play with Legos, don't they?"

"Yeah, well, Dad should be home soon, anyways," Dean said. It was something he said a lot, and Sam miraculously still believed him most of the time.

"Yeah...."

Dean's eyes drifted back towards the recently unveiled box. He thought of the dwindling faith in Sam's voice, and his expression darkened. "Y'know what, Sam? Let's play it."

" _You_ want to play _Pretty Pretty Princess_?" Sam asked, incredulous. "What would Dad think if..." he trailed off. The glint in his eye told Dean that he'd caught on. "Okay. Yeah. Sure, let's play."

Dean lifted the lid, and Sam tore into the bags containing all of the cheap plastic pieces with a savagery that Dean had never seen in him before.

"I'm blue." Dean snatched up the colored pieces to claim them before Sam could.

"I'll be purple," Sam said, absently grabbing the purple playing piece while simultaneously trying to read the instructions he held in his other hand. "But we're gonna have to put all of the stuff back in the middle of the board, anyways. We don't start with any of it."

"What's the point, then?" Dean asked, depositing handfuls of plastic necklaces and bracelets into the container.

"We're supposed to use the spinner to move around the board and collect all of our color of jewelry and the crown." Sam turned over the round lid to the container and absently flicked the plastic spinner on the underside. "And... that's it. That's the whole point."

Dean looked at the spinner, then at the mound of jewelry in the middle of the board. "This is so freaking dumb," he said. A sudden grin split his face.

"Yeah. Wanna start?" Sam asked.

"First, I'm gonna establish _our_ rules, Sammy," Dean said. He sat up straighter, then held up his fingers. "One: we have to wear every piece of jewelry we get. Crown and all, no matter how stupid or girly we look. And two: the prettiest princess gets the last bowl of Lucky Charms."

Sam gave a solemn nod in agreement.

The motel heater kicked in right after they placed the markers representing their positions on the board. Then Sam gave the spinner a determined flick, and the game began.

It took a moment for Sam to find the object he was looking for in the already-tangled mess of plastic beads. But he managed to fish it out and slide it onto his finger, and the two of them eyed it. "Dunno why the black ring is bad," Sam said, spinning it around. "It's the least ugly looking piece of jewelry in the entire game."

Dean wore a satisfied smirk. "Off to a great start, Sammy." He flicked the plastic arrow hard enough that it bent and wobbled as it spun.

By the time Dean had a bracelet, a necklace, one clip-on earring, and the crown, both of them were giggling a little. It was a surreal feeling, just sitting around playing a board game like this. They'd never really owned one before. Board games took up too much space and too much time, and they often needed at least three players to really be fun.

"These earrings are pinching my ears," Sam complained. He had both of them on, and he pawed at them every minute or so, adjusting the clamps.

"Never thought you'd be one to give up, Sammy," Dean said. His single earring was admittedly a little uncomfortable, but there was no way he was letting Sam know that.

"Who said anything about giving up?" Sam crossed his arms.

A few turns later, Dean gleefully handed the black ring back to Sam, then whooped and shouted "I win! Who's the prettiest princess, Sammy?"

"You are," Sam grumbled. He shook his head like a dog, and the earrings flew off his ears and flew several feet away. But Sam was smiling, and Dean just smiled wider and leaned back. Stupid girly game or not, winning felt good.

They played the game three more times before John showed up. Each time, the stakes got sillier and sillier until the prettiest princess was winning an imaginary unicorn steed that gored all of its enemies with its bronze war-horn.

After the third game, Dean and Sam both knew their luck was trickling away very fast.

"We have to get rid of the box," Dean said. "It's too big to hide."

"We can fit most of the pieces in the container. Except for the board. I'll take one, and you take the other. If we split them up, there's less of a risk he'll find them both."

Dean ended up hiding the container full of plastic jewelry in his own duffel, and Sam hid the pieces of the playing board in his. They discarded the exterior box in one of the dumpsters in the parking lot outside of the motel, and Dean slipped away to return the other stolen presents, unwrapped, to the house he'd taken them from. It was better John didn't ask too many questions.

Neither of them suggested they keep the game, in so many words. They both just came to a nonverbal agreement about it, quiet and furious about something that neither one of them wanted to name.

Then John came back, and Dean was his faithful soldier as always, except this time Sam _knew_ , and somehow everything was just a little _different_.

Some weeks passed before they played the game again. John was on his way out the door, Dean meekly lowered his gaze and said " _yes sir_ ," and then the Impala's tires were grinding gravel into the dirt, and Dean stormed back into the motel room, walked over to his duffel, then set the container of jewelry onto the table with an audible sound.

But Dean was smiling again when Sam placed the crown very lopsidedly on his head. They decided a rival prince had tried to have him assassinated only for the sharpshooter to miss his shot and only manage to dislodge the crown. Later, the prince also made an attempt at Dean's life by bestowing upon him a cursed ring.

Then, in immediate succession, Sam had to take the ring, and Dean got to take the crown, which won him the game. Story-wise, they decided that Sam took the curse upon himself and then left Dean his kingdom after his death. Dean used the sudden boost in political power to take revenge on the prince by impaling him on the horn of his war unicorn. Then he revived Sam and split their combined kingdoms between them again, and the two of them returned all of the jewelry to the middle and played it again.

John showed up only twenty minutes after they had put up the game. Dean's heart beat in his throat when he imagined what would've happened if John had arrived just a little earlier.

Once, they played a game when they had only a half-hour timeframe, if that. Dean's fingers shook with adrenaline all through the last few turns. Sam's eyes kept darting towards the window, and he winced at the sound of every car pulling into the parking lot.

Pretty Pretty Princess was a lot of things, but most of all, it was a game of risk.

It was the first thing Sam and Dean did after John left, and it was often one of the last things they did before he got back.

Sometimes, when they were feeling particularly daring, the stakes got higher. One time, they decided that the loser had to leave the motel room and buy the winner a candy bar from the vending machine while still decked out in his jewelry.

That time, Dean strode through the door with cheeks pink from the crisp winter air and his jacket proudly open to reveal two necklaces around his neck, one bright blue and cheap and garish, the other a handsome black cord with a brass pendant dangling from it, and Sam's eyes caught on both of them.

Dean just grinned and tossed him the candy.

It was inevitable that some of the game pieces would get lost over time. The purple playing piece disappeared somewhere between Minnesota and Mississippi, and Sam begrudgingly agreed to play as green for maybe four games before he decided to just use an army man as a replacement playing piece and wear the purple jewelry like he always had.

Next to go after that was: one purple and one blue earring, the pink bracelet, the green ring and the green necklace, the blue ring, the purple bracelet, and two of the three remaining playing pieces. Scattered across the U.S., John Winchester had unknowingly left a broken trail of plastic jewelry in crap motels.

To make the game still fair and playable, Sam used the green jewelry to replace the missing purple items, and Dean did the same with the pink jewelry to complete the blue set. They both played with army men to mark their places on the board. Somewhere along the way, Dean and Sam decided that the army men were working undercover to solve a very important case and save lots of lives.

But sometimes, Pretty Pretty Princess became a very dangerous game.

One night, John came back late and passed out drunk on the couch, the television blaring bright and obnoxious in front of him.

Sam looked at John in disgust, then he caught Dean's eye, and very slowly, he reached over and unzipped his duffel and brought out four somewhat battered cardboard pieces. Sam sat down in the narrow gap between their beds, then he laid out the game board on the awful shag carpet and stared defiantly up at Dean.

They played their quietest game of Pretty Pretty Princess yet. Neither of them said a word. They both gave the plastic arrow a very delicate spin, and took care not to disturb the jewelry in the container too much whenever they had to reach into it.

Dean's heart thumped a steady, brusque rhythm the entire time. He glanced up at every opportunity to check that John's head was still against the armrest, that his snoring was still regular and even.

When Sam won, he just smiled wide and dangerous, and Dean couldn't help but smile back at him, trading one mischievous smirk for another. Then John drunkenly mumbled something, and Sam's face blanched, his smile falling rapidly, and both of them hurriedly removed the jewelry and stuffed it back where it was safely hidden, and by the time John was standing and stretching, Sam and Dean were seated on separate beds, Dean flipping through an old comic book, Sam enthralled with some novel.

But sometimes, they played a safer game. When they knew John would be gone for at least a couple days, when it was more something to play out of boredom than defiance.

Those days, Dean sometimes let himself pretend. Because it was kind of nice to be pretty, even though he knew that in reality, the jewelry looked ridiculous. It was the _idea_ of it that counted, really. And besides, Sam looked adorable in it. Sam, who sat with a contemplative expression on his face like this was a freaking chess tournament requiring amazing feats of logic and a great deal of philosophizing.

"You trying to cheat?" Dean asked, trying not to stare too fondly.

Sam looked at him. "What?" He blinked. "Dean, how would I even cheat at this game?"

"I know you could think of something. You could just sit there and look all cute and then nudge your guy an extra space when you think I'm not paying attention."

"You think this makes me look cute?" Sam asked. His tone was indecipherable, and Dean couldn't tell if Sam was taking it as a compliment or if he was bothered by it.

So Dean just shrugged. "You're still a little kid. Even if you're a boy, any kid in bad dress-up looks cute. If I was an old lady, I'd be pinching your cheeks." Dean reached over and pinched him anyways.

"Hey!" Sam jerked his face out of Dean's reach. He glared up at Dean, then reached into the pile of jewelry and pulled out the lone remaining purple earring, clipping it to his ear. "Or I could just beat you fair and square," he said, triumphant.

"The prettiest princess gets to submit to the invading army," Dean said. He clambered over and tackled Sam to the ground.

"That wasn't‒" Sam laughed and writhed on the floor as Dean tickled him. "‒Part of the conditions." His crown slid off and rolled a few feet away. "Dean, stop!" he panted, trying to push Dean off of him.

Dean reached over and snatched up the crown, putting it on his own head while he kept Sam pinned. "Looks like the coup was a success, Sammy," he said.

The carpet was dusty and smelled a little like sour milk, but as he lay there, Sam's laughter turned into genuine giggles, and he shoved half-heartedly at Dean. "That crown almost makes you look actually pretty," he said.

"It's just cheap plastic," Dean said.

"Yep," Sam agreed.

"Are you saying I'm cheap?" Dean's eyebrow lifted.

Sam shrugged innocently. "Just said you were pretty, is all." He grinned. Dean moved off of him, and he sat up. "Wanna play again?" Sam asked.

"Eager to retake your crown, huh?" Dean picked up the army men and righted them again.

"Never lost it in the first place. That happened after the game, which means it doesn't count," Sam said, putting handfuls of spilled jewelry back into the container. He made a face. "Dean, you bent the board!" he pointed at the sizable fold that had appeared in the cardboard.

Dean looked at it. "It's not too bad," he said.

Sam frowned. Then he sighed. "Well, I guess‒"

And that's when the motel door opened.

Dean could read the look of horror plain as the brightest day on Sam's face, but he could not decipher the expression that their father wore.

"Dad‒" Dean's voice broke. Then he remembered that he was still bedecked in plastic jewelry, and he shed it as fast as he could. "I can explain. We were just‒" His hand was shaking as he reached up to knock off the crown.

John's back was towards the setting sun, his face mostly in dull shadow. His eyes surveyed the scene on the floor, but he said nothing.

"It's just a game," Sam said, his voice cold.

"Shut up, Sammy," Dean snapped. If John's wrath came down on them for this, Dean needed to be the one who took the brunt of it. "It was my idea, Dad. I was the one who found it, and the game was so stupid, I forced Sammy to play it 'cause I dared him, and‒"

"I thought," John started, and he spoke slow and quiet and even, though his words carried easily, as the motel room had grown painfully still. "I thought I had two boys," John said.

It was all over. Dean felt something prickling in his eyes and sitting heavy in his stomach, and he wanted to cry, but he knew that if he did that, it would only make everything worse. "Dad‒" he tried, but there was nothing he could say.

"Come here, Dean. There's something I want to show you."

Even after standing up, Dean felt like he was groveling. He tried to hold his head up high, but he couldn't quite bring himself to meet John's eyes again, so he mostly just looked towards the floor at his father's feet.

"You come too, Sam. Pick up that mess first, and bring it here."

There was a noise of plastic rustling against plastic. Then Sam was getting to his feet somewhere behind Dean, and John opened the door. John took the components of the game from Sam as Sam and Dean walked past him.

He led them out to where the Impala stretched beneath a couple spindly trees.

"Get in."

They drove for a couple miles. John pulled over when they reached an empty field that had maybe once been farmland, the land bearing grooves in the dirt that appeared to be long-overgrown furrows.

As soon as they had waded deep enough into the shallow brush of weeds underfoot, John ordered Sam to stand several paces away. Dean turned, then almost managed to dodge out of the way as John slammed into him and tackled him roughly to the ground.

"Your form is sloppy, Dean," John said, "If I was a monster, you'd be dead."

Dean struggled, wrestling with John, but he couldn't find an opening to free himself.

"Not good enough," John said. "You let yourself get caught off guard, and now you're paying for it."

Something scraped a thin gash into Dean's arm as he thrashed under John. But he managed to wriggle free, and he was standing and opening his mouth to say something when John's knuckles impacted with his chin.

When the fuzziness cleared, Dean was seated roughly on the ground, his arm oozing wet and hurting, and Sam was right there, his gaze drifting from concern aimed at Dean to daggers aimed at John.

"You're still too slow. I expect you to be able to escape me sooner next time. If you had spent your time training like I had ordered, we would be past this now," John said. He tossed a cloth at Dean.

The scratches on Dean's arm stung as he dabbed at them with the cloth. "That hurt," he muttered, knowing as he said it that it was a mistake.

"Then quit your bitching and take it like a man."

For a minute, none of them said anything. Dean tried to keep his breath from hitching too audibly as his arm and face throbbed.

"Because you know what happens to women and girls and sissies? They die," John said flatly. "Your mom did. Bobby's wife. Those girls the werewolf killed a few towns back. That limp-wristed boy with the ghost. And that's why it's our job to protect them."

"I understand," Dean said.

Sam stood up. "So are you going to hit me, now, too?" he asked.

"No. You're not ready for that sort of training," John said. "I have a different lesson in mind for you."

He turned and fetched something that Dean could not see.

"Sam, you know the theory behind killing ghosts, don't you?" John asked. Sam nodded, and John continued, "And you've read about haunted objects, right?" Sam nodded again. "Show me," John ordered. "I want you to treat this like it's a haunted object."

John held something out in front of him, and this time Dean saw quite clearly what it was, recognizing the familiar shapes and garish colors: it was the Pretty Pretty Princess game.

The jewelry rattled as Sam took it from John. Sam crouched down, and his bangs swooped into his eyes. He brushed them aside absently, then placed the game onto a bare patch of dirt. He sprinkled salt over the plastic and cardboard, the grains sparkling like glitter in the descending dusk. Then he dribbled gasoline over the cardboard and poured it into the container.

It took Sam several tries to ignite the lighter. He chewed the corner of his lip as he squeezed the button and rolled the wheel with his nail.

After a flame emerged from it, small and yellow and blue, Sam held the lighter over the game and hesitated for just a moment before his fingers were releasing it and it was falling, tumbling and wobbling through the short distance to the ground.

The flames caught the thirsty cardboard at once. The plastic burned less eager, but the gasoline kept the fire alive, and soon the vibrant colors were warping and mixing, contorting into broken shapes.

Plastic has a certain smell to it as it melts. Something strong and pungent and smooth. It filled Dean's nose, clouded out his thoughts.

The molten crown dribbled down the sides of the container, and the last piece of jewelry to remain relatively solid was the black ring in the dead center.

**Author's Note:**

> I wrote a "sequel" to this fic, but it does not take place in the canon 'verse, largely because I don't think I can really imagine these characters being able to actually resolve these issues in the currently existing show canon.
> 
> The "sequel" is titled [A Kingdom for a Necklace](http://archiveofourown.org/works/4176480), and it's part of a post-season-five AU 'verse wherein (not soulless) Sam and Dean (with some help from Cas) raise the shifter baby Bobby John (from episode 6.02 "Two and a Half Men"). That's all you really need to know to be able to understand the fic.

**Works inspired by this one:**

  * [A Kingdom for a Necklace](https://archiveofourown.org/works/4176480) by [Fallynleaf](https://archiveofourown.org/users/Fallynleaf/pseuds/Fallynleaf)




End file.
